CandleKeep

Lenny's Newsletter — Complete Archive

by Lenny Rachitsky

lennynewslettereducationvalue
Pages2117
Formatmarkdown
ListedMarch 18, 2026
UpdatedMarch 18, 2026
Subscribers44

About

Complete archive of 349 Lenny's Newsletter issues (2020-2025). Covers product management, growth, startups, leadership, hiring, strategy, and career advice from top PMs and operators.

467Chapters
5002Topics
2117Pages

Preview

How to build your PM second brain with ChatGPT (2025-12-16)

👋 Hey there, I’m Lenny. Each week, I tackle reader questions about building product, driving growth, and accelerating your career. For more: Lennybot | Lenny’s Podcast | How I AI | Lenny’s Reads | AI/PM courses | Public speaking course

Annual subscribers get 19 premium products for free for one year: Lovable, Replit, Gamma, n8n, Bolt, Devin, Wispr Flow, Descript, Linear, PostHog, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, ChatPRD + Stripe Atlas (while supplies last). Subscribe now.

Someone smarter than me once said, “AI won’t replace you, but a person using AI better than you might.” I believe this is exactly right. Right now, we all need to be building the skills that help us become that person using AI better. Lucky for us, Amir Klein is already that person and has written a guide for the rest of us. Though it’s targeted at product managers, the advice and workflows can be implemented by anyone in any function. Thank you, Amir, for giving us a glimpse into the future and the concrete steps to get there.

For more, follow Amir on LinkedIn. You can also listen to this post in convenient podcast form on Spotify / Apple / YouTube.

The first month in my new role at monday.com, I was tasked with building our first AI agent. The goal was to create an AI co-pilot, something users could turn to for insights, explanations, or building complex workflows they wouldn’t know how to create on their own. To build that, I needed a ton of context—all the internal knowledge, decisions, assumptions, and scattered inputs that shape any product direction. And gathering all of that felt completely overwhelming.

I was drowning.

All that context lives everywhere: Slack channels, Notion pages, Monday boards, decks, Google Docs. Hundreds of tiny fragments I could never quite piece together. I kept running into mental blocks, forgetting what I knew from where, and getting stuck. Instead of trying to keep all of that context in my head like I always had, this time I wanted to try something new. I dumped everything I had into a ChatGPT Project, word-vomited all that was on my mind, and asked if it could help me get started. And boy, did it.

Finally, I felt like I could smell a roadmap on the horizon, a direction was forming, and things began to click. Even better, I felt somewhat in control without being stressed about storing everything in my head. I could store it in the AI instead—a second brain. Instead of all that information overloading my own brain and pulling my attention in a hundred different directions, I could finally focus on the product work I love and need to get right to be successful: understanding the problem, shaping the vision, and building something meaningful.

My good friend Tal taught us how to think with AI. I’m building on Tal’s post by showing what happens when AI becomes an extension of your mind—when it carries your context, grows alongside you, and ultimately amplifies what you’re capable of as a PM.

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Table of Contents

A year free of PostHog ($16,500 value): The all-in-one analytics, experimentation, feature flag, surveys, session replay, error tracking, data warehouse, LLM analytics platform (2025-12-02)

Part 2 of how to get the most out of your product pass—and welcome, Stripe Atlas, to the bundle! (2025-11-04)

How to get the most out of your product pass, part 1 (2025-09-23)

Taking the week off + a newsletter cadence update (2025-08-26)

How tech’s most resilient workers handle burnout (2025-06-17)

**Where to go from here**
Taking the week off (2025-06-03)
How tech workers really feel about work right now (2025-05-27)

Announcing the greatest product bundle ever: Get a year free of Granola, Notion, Superhuman, Linear, and Perplexity with an annual subscription (2025-02-04)

Taking the week off 🎄🕎🎁 (2024-12-31)

Get Perplexity Pro free for 1 year (2024-09-23)

Announcing the Lenny & Friends Summit 🙌 (2024-07-29)

Taking the week off (2024-07-16)

Meet your Lenny’s Newsletter Fellows ✨ (2024-07-01)

How to use Perplexity in your PM work (2024-06-11)

Taking the week off (2024-05-28)

How Perplexity builds product (2024-04-30)

How Gong builds product (2024-01-23)

Taking the week off (and thank you!) (2023-12-26)

The Best of Lenny’s Newsletter 2023 (2023-12-12)

Skipping newsletter today (2023-10-10)

How Linear builds product (2023-09-26)

How Shopify builds product (2023-07-25)

How Snowflake builds product (2023-07-11)

How a traumatic brain injury made me a better PM—and person (2023-06-06)

How Notion builds product (2023-05-30)

How Ramp builds product (2023-05-23)

How Miro builds product (2023-05-09)

How to use ChatGPT in your PM work (2023-04-11)

Taking the week off (2023-04-04)

How Duolingo builds product (2023-03-21)

I built a Lenny chatbot using GPT-3. Here’s how to build your own. (2023-02-07)

How Coda builds product (2023-01-31)

The Best of Lenny’s Newsletter 2022 (2022-12-27)

How Figma builds product (2022-11-15)

Taking the week off (2022-10-04)

Taking the week off (2021-12-21)

Taking the week off (2021-10-19)
60 ideas to boost your growth (2021-10-12)

The 10 commandments of salary negotiation (2021-09-24)

How behavioral science can boost your conversion rates (2021-09-17)

Five habits of highly annoying product managers (2021-08-10)

Choosing Your North Star Metric (2021-06-16)

Why marketplaces fail (2021-04-13)

The PM 🤝 Design Partnership (2021-03-23)

Positioning (2021-01-26)

Increasing team velocity (2021-01-12)

Pricing your SaaS product (2020-10-27)

What it feels like when you've found product-market fit (2020-09-29)

When to hire your first product manager (2020-09-15)

Getting better at product strategy (2020-09-08)

**First, how does one measure retention?**

**First, how does one measure retention?**

My favorite product management templates (2020-08-04)

In summary

Winning at SEO (2020-07-14)

How today's fastest growing B2B businesses found their first ten customers (2020-07-07)

**Inspiration for the week ahead 🧠**
Evaluating a (marketplace) business idea (2020-06-23)

Evaluating a (marketplace) business idea - Issue 31 (2020-06-23)
Q: I loved your series about [kickstarting and scaling a marketplace business](https://www.lennyrachitsky.com/p/how-to-kickstart-and-scale-a-marketplace). As an investor, I’m curious how you evaluate marketplace business ideas. What do you look for?

One team, one roadmap - Issue 30 (2020-06-16)

What is good retention? (2020-06-09)

In summary

How the biggest consumer apps got their first 1,000 users (2020-05-12)
👉 [Updated version of this post here](https://www.lennysnewsletter.com/p/consumer-business-find-first-users) 👈

Setting goals - Issue 23 (2020-04-29)

Setting goals (2020-04-28)

How To Know If You're Supply or Demand Constrained 🤹‍♂️ - Phase 2 of Kickstarting and Scaling a Marketplace Business (2019-12-10)

The Secret to a Great Planning Process — Lessons from Airbnb and Eventbrite (2019-09-26)

**Step 2: Align on the problem with your team and stakeholders**
**Step 3: Keep coming back to the problem**
**A final note**
How to get into product management (2019-06-14)

Plan the How: The four most common paths into PM

What Buddhism Taught Me About Product Management (2019-06-14)
1. There is suffering 😨
2. All things are impermanent ❄️
3. There is no lasting self ⛄️

Create strong culture, values, and rituals
**Nail the problem statement**
Set wildly ambitious goals
Start with the ideal and work backward

Maintain a high bar for everything

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